Dichloromethane → 1-(3-Sulfamoylphenyl)-1H-pyrazolo[3,4-b]pyridin-4-ylboronic acid

HRID 1186790Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:11]3[CH:12]=[C:13]([S:17]([NH2:20])(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:9]=[CH:10][C:3]=12.CC1(C)C(C)(C)[O:25][B:24](B2OC(C)(C)C(C)(C)O2)[O:23]1.C([O-])(=O)C.[K+].C(Cl)Cl>CS(C)=O>[S:17]([C:13]1[CH:12]=[C:11]([N:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([B:24]([OH:25])[OH:23])=[C:3]3[CH:10]=[N:9]2)[CH:16]=[CH:15][CH:14]=1)(=[O:19])(=[O:18])[NH2:20]

Participants

Conditions

Temperature: 84 °C

Procedure

To a 48 mL pressure bottle was added 3-(4-iodo-1H-pyrazolo[3,4-b]pyridin-1-yl)benzenesulfonamide, “dot” 2 1-methyl-2-pyrrolidinone complex (60 mg, 0.100 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (94.7 mg, 0.373 mmol), potassium acetate (24.4 mg, 0.249 mmol) and anhydrous DMSO (Volume: 2 mL). The reaction mixture was purged well with argon and treated with PdCl2(dppf).CH2Cl2 (12.5 mg, 0.017 mmol). The reaction mixture was then heated to 84° C. for 1 h to give the desired intermediate. LC/MS (Condition B): ret. T=2.4 min, (M+H)+ 318.98.

Workup

customThe reaction mixture was purged well with argon
additiontreated with PdCl2(dppf)

Sources & evidence

ORD record: ord-1e76399b7ba24a718af6a74a4c700551
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673922B2

Reaction notes

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